Water → 3-Ethenyl-5,6-dihydrofuro[2,3-c]pyridazine

HRID 15179Notes

Reaction equation

HRID 15179 reaction equation
FC(F)(F)S(O[C:7]1[N:12]=[N:11][C:10]2[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].B1(C=C)OB([CH:30]=[CH2:31])OB(C=C)O1.C1C=CN=CC=1.O>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:30]([C:7]1[N:12]=[N:11][C:10]2[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1)=[CH2:31]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 866141565,6-Dihydrofuro[2,3-c]pyridazin-3-yl trifluoromethanesulfonate

Product 1

HCID 675273573-Ethenyl-5,6-dihydrofuro[2,3-c]pyridazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5,6-dihydrofuro[2,3-c]pyridazin-3-yl trifluoromethanesulfonate (500 mg, 1.85 mmol) in dimethoxyethane (20 ml) was degassed then treated with tetrakis(triphenylphosphine)palladium (0) (116 mg), potassium carbonate (257 mg), 2,4,6-trivinylcyclotriboroxane pyridine complex (for a preparation of this reagent see F. Kerins and D. F. O'Shea, J. Org. Chem. 2002, 67, 4968-4971) (416 mg) and water (3.6 ml). The mixture was stirred at 80° C. for 2 hours then partitioned between DCM and saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with 10% methanol in DCM then the combined organic extracts dried and evaporated. The residue was chromatographed eluting with ethyl acetate affording a white solid (111 mg, 36%).

Workup

  1. customfor a preparation of this reagent
  2. customthen partitioned between DCM and saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted with 10% methanol in DCM
  4. customthe combined organic extracts dried
  5. customevaporated
  6. customThe residue was chromatographed
  7. washeluting with ethyl acetate affording a white solid (111 mg, 36%)

Sources & evidence

ORD record
ord-bec46baf34f44f1f884d7e5c93337c07
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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